Azodyestuffs and process of making same



Patented Apr. 27, 1926.

UNITED STATES PATENT OFFICE.

-GUILLAUME DE MONTMOLLIN AND GERALD IBQNHfiTE, F BASEL, SWITZERLAND, AS-SIGNORS TO THE SOCIETY OF CHEMICAL INDUSTRY IN BASLE, OF IBASEL,SWITZER- LAND.

AZODYES'IUFFS AND PROCESS OF MAKING SAME.

No Drawing.

To all whom it may concern:

Be it known that we, GUILLAUME on MoNTMoLLIN and GERALD Boumirn. bothcitizens of Switzerland, reslding at Basel,

Switzerland, have invented newand useful Azodyestufi's and Process ofMaking Same, of which the following is a full, clear, and exactspecification.

The invention relates to the manufacture of valuable new azodyestufi'swhich may be produced on the fibre. It comprises the new dyestuffs, themanufacture of same and the material on which the new dyestuffs havebeen developed.

- Application filed March 23, 1925. Serial No. 17,834.

It has been found that bordeaux to blue and black azodyestufi's withexcellent fastness may be obtained bycoupling-hydroxynaphthalene-l-arylketone With tetrazo-compounds of thegeneral formula:

wherein R and R stand for equal or different aromatic residues.

The dyestuffs thus obtained, correspond with the general formula inwhich R and R stand for the residues already mentioned and R and R mean-hydroxynaphthyl-l-arylketone residues,

30 form dark powders insoluble in water, dissolving in acetic acid andalcohol from red to brown and blue, in concentrated sulfuric acid togreen solutions, which dyestuffs may be employed for the production oflakes;

35 prepared on the fibre they yield bright bordeaux to blueand blackshades.

Example 1.

The new dyestufi corresponds most probably with the following formula:

Example Q.

Cotton is impregnated with an alkaline solution containing 15 gr. of4-hydroxynaphthalene-1-pl1enylketone per liter and passes through a bathof tetrazotized 4.4- dia-mino 3' methoxy 6 metliylazobenzene neutralizedwit-h sodium acetate. The cotton is thus dyed full, fast reddishmarineblue tints.

Ewample 3. The material to be printed is padded with In the followingtable the shades of some of the dyestuffs which may be produced oncotton according to the present invention are given.

Diazotization component. Shade Coupling component.

p-nitranillne-i-a-naph- 4-hydroxynaphtha- Dark bluish-viothylamine,reduced. lere-l-phenylketone. o

p-nitraniline+o-anisi- Dark violet.

dlne, reduced. p-nitroo-chloroaniline do Violet.

+p-cresidine, recluced. p-mtro-o-anls1dine+ando Do.

lline, reduced. pitro-o-anisidlne+ do Reddlsh dark esidine, reduced.blue. m-ni-tranilin+cresldine, do Blulsh-violet.

reduced. p-am1noacetanillde+ do Reddlsh marinecresldine, saponified. ue

Do -hydroxynaphtha- Marine-blue. Iene-1-(2-c 111 or o)- phenylketone.Do- 4.4-di h ydroxy-1.1- Black. dinaphthylketone. p-mtraniline+aniline,4-hydroxynaphtha- Dark bordeaux.

reduced. lene-l-phenylketone. p-111tramline+ .-naphdo Dark violet.

thylamme, reduced.

What we claim is: 1. As new products'the herein described newazodyestufis of the general formula.

and R and R, for a t-hydroxynaphthalene l-arylketone residues, whichdyestuffs form dark powders insoluble in water, dissolving in aceticacid and alcohol from red to brown and blue, in concentrated sulfuricacid to green solutions, which dyestuffs may be employed for theproduction of lakes; prepared on the fibre they ield bright bordeaux toblue and black s ades.

an alkaline solution containing 15 gr. of 4-hydroxynaphthalene 1phenylketone per liter. After drying the material is printed with aprinting color containing 13.1 parts of the reduced tetrazotizedazodyestuff from diazotized m-nitraniline and a-napht-hylamine perliter. The dark violet dyeing develops rapidly and is very fast.

The new .dyestufi' corresponds most probably with the following formula:

2. As new products the herein described new azodyestufi's of the generalformula wherein R and R stands for arylresidues and R and R for a4-hydroxynaphthalenel-phenylketone, which dyestuffs form dark powdersinsoluble in water, dissolving in acetic acid and alcohol from red tobrown and blue, in concentrated sulfuric acid to green solutions, whichdyestuffs may be employed for the production of lakes; prepared on thefibre they yield bright bordeaux to blue and black shades.

' 3. As new products 'the herein described new azodyestuifs of thegeneral formula.

wherein R and R stand for aryl residues of the benzene series, and R andR for the 4- hydroxynaphthalene-l-phenylketone, which dyestuffs formdark powders insoluble in water, dissolving in acetic acid and alcohol Ifrom red to brown and blue, in concentrated sulfuric acid to greensolutions, which dyestuffs may be employed for the production of, lakes;prepared on the fibre they yield bright bordeaux to blue and blackshades.

5. The material dyed with the dyestuffs of claim 1, said dyestuffs beingdeveloped on the material.

6. The material dyed with the dyestuffs of claim 2, said dyestuffs beingdeveloped on the material.

7 The material dyed with the dyestufls of claim 3, said dyestuffs beingdeveloped on the material. 8. The material dyed with the dyestuffs ofclaim 4;, said dyestuffs being developed on the material..

In Witness whereof We have hereunto signed our names this 11th day ofMarch, 1925.

GUILLAUME DE MONTMOLLIN.

GERALD BONHOTE.

